Most coworkers are great; the work can be interesting; management is clueless, harmful, dead weight
Pros
Most coworkers are really smart, hard working, friendly, thoughtful, and looking out for each other. Every day is different and you get to use your brain solving real problems in a way that will have a real impact. The industry and the product are interesting. Having an automatic employer 401k contribution plus a 401k match is nice.
Cons
Most middle management is dead weight or or a burden on their team. Very little direction and leadership is provided so most project flounder but then blame gets placed on those who were trying to muddle through the undefined work. It's nearly impossible to get a timely, relevant, sufficiently-nuanced answer out of leadership. Employees are not empowered to make decisions that enable them to do their jobs. Work is smothered in poorly defined, ever-changing, top-down processes. The company is extremely contractor- and consultant-heavy with some teams being outnumbered 5 to 1, outside people to United people, so the people who know things about the business, industry, processes, or tools spend the bulk of the time explaining to six-month swoop-in-swoop-out workers how things work and why things are the way they are rather than doing actual productive work. Many, many functions are outsourced to people who do exactly as they're told, even when what they're told is obviously a mistake or terrible idea – they lack the peripheral vision and/or investment in work and/or experience and/or empowerment to say "are you sure?" – which causes many, many last minute fire drills and sub-par business outcomes. Many leadership types will listen to your concerns and re-assure you and then do nothing with the substance of those conversations. Re-orgs, with RIFs and confusion, happen on an annual basis and are designed by people who don't actually know what work is going on so the new org structures never reflect the realities of the organization so get half-implemented, leaving an even bigger mess for the next re-org. Health insurance options change every year. HR and other employee benefits (travel, discounts) are extremely opaque in communication: the information is out there but you must wade through 2012, 2013, 2014, 2015, 2016 information from different subsidiaries and work groups spread across dozens of different intranet and answer systems to get an answer only to find out what you're looking at is obsolete. Pay is stagnant. Opportunity for advancement is non-existant. Employee recognition and other "look how much we care about you!" things only make it to Chicago HQ employees, not other Chicago locations, Houston, Denver, or other places. Oscar's message of hope and change rings hollow – leadership only cares about agents and flight attendants. Flight benefits are very over-hyped. You can fly for cheap-ish, but you can't actually get on a plane to do so.